What is the reason behind Chicago Cubs took so long to win the world series.
During the Wrigley family ownership, while initially invested in winning, over the years as newer generations of Wrigley took over, it became more and more of a business. From a pure business perspective, it made little sense to spend more money for no real financial gain.
As true as that was under the later generations of Wrigley ownership, it became achingly true once the team was purchased by the Chicago Tribune. Check out the marvelous collection of Chicago cubs hats and Chicago cubs shirts.
Throughout those times, there some great folks that came and went that tried their best to put together a winning team given the restrictions they were under. Dallas Green was perhaps the greatest example of that. Dallas was the GM of the Cubs from 1981 to 1987. He scoured the league for bargains. Players that were no longer in their prime, but were still amazingly gifted were one of his strategies.
All of this changed when Tom Ricketts purchased the club in 2009. Now there was an owner that cared about winning. Since then he has invested in finding the right leadership - Theo Epstein as President of Baseball Operations, and seasoned head coach Joe Maddon. Since then they have made smart moves in trades and free agency, but maybe most importantly have really built their farm club system into a machine, producing star after star.